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Details

Stereochemistry ACHIRAL
Molecular Formula C10H13NO2
Molecular Weight 179.2157
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENACETIN

SMILES

CCOC1=CC=C(NC(C)=O)C=C1

InChI

InChIKey=CPJSUEIXXCENMM-UHFFFAOYSA-N
InChI=1S/C10H13NO2/c1-3-13-10-6-4-9(5-7-10)11-8(2)12/h4-7H,3H2,1-2H3,(H,11,12)

HIDE SMILES / InChI

Molecular Formula C10H13NO2
Molecular Weight 179.2157
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Phenacetin was used as an analgesic and fever-reducing drug in both human and veterinary medicine for many years. Since a major portion of a dose of phenacetin is rapidly metabolised to paracetamol, it seems possible that phenacetin owes some of its therapeutic activity to its main metabolite, paracetamol, whereas its most troublesome side effect (methaemoglobinaemia) is due to another metabolite, p-phenetidine. Phenacetin was shown to inhibit cyclooxygenase (COX)-3, a cyclooxygenase-1 variant while p-phenetidine potently inhibits both COX-1 and COX-2. There is sufficient evidence in humans for the carcinogenicity of analgesic mixtures containing phenacetin. Analgesic mixtures containing phenacetin cause cancer of the renal pelvis, and of the ureter. Phenacetin was withdrawn from many analgesic mixtures long before the legal ban in several countries.

CNS Activity

Originator

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phenacetin
PubMed

PubMed

TitleDatePubMed
IS PHENACETIN A NEPHROTOXIN?A REPORT ON TWENTY-THREE USERS OF THE DRUG.
1964 Aug
Analgesic abuse, ureteric obstruction, and retroperitoneal fibrosis.
1975 Apr 12
The induction of renal papillary necrosis in Gunn rats by analgesics and analgesic mixtures.
1975 Feb
Epidemiology and etiology of premalignant and malignant urothelial changes.
2000
Rate-determining steps in phenacetin oxidations by human cytochrome P450 1A2 and selected mutants.
2000 Sep 19
Xpa and Xpa/p53+/- knockout mice: overview of available data.
2001
[Determination of three components in compound chlorophenamine tablet by iterative target transformation factor analysis].
2001 Apr
Detailed characterization of experimentally derived human hepatic CYP1A1 activity and expression using differential inhibition of ethoxyresorufin O-deethylation by fluvoxamine.
2001 Aug
Role of cytochrome P450 isoenzymes in metabolism of O(6)-benzylguanine: implications for dacarbazine activation.
2001 Dec
Analysis of the phase solubility diagram of a phenacetin/competitor/beta-cyclodextrin ternary system, involving competitive inclusion complexation.
2001 Jan
Relationship between nonphenacetin-combined analgesics and nephropathy.
2001 Jun
Interindividual variations in levels and activities of cytochrome P-450 in liver microsomes of Chinese subjects.
2001 Mar
Trends of analgesic nephropathy in two high-endemic regions with different legislation.
2001 Mar
Suppression of agglomeration in fluidized bed coating. IV. Effects of sodium citrate concentration on the suppression of particle agglomeration and the physical properties of HPMC film.
2001 Mar 14
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Differential inhibition of human CYP1A1 and CYP1A2 by quinidine and quinine.
2001 Nov
[Optimal conditions for extraction of "caffetin" and "saridon" tablet components from aqueous solutions].
2001 Nov-Dec
A case of phenacetin-induced skin cancer in Hong Kong.
2001 Sep
Renal PGE2 production in the human and rat following phenacetin, acetaminophen and p-aminophenol.
2002
Drug-induced hepatitis with hepatic granuloma due to saridon.
2002
Alteration of phenacetin pharmacokinetics after experimental spinal cord injury.
2002
Fondaparinux sodium is not metabolised in mammalian liver fractions and does not inhibit cytochrome P450-mediated metabolism of concomitant drugs.
2002
Comparison of vasoconstrictor responses to selected NSAIDs in rabbit renal and femoral arteries.
2002
Phenacetin O-deethylation in extrahepatic tissues of rats.
2002 Apr-Jun
Evaluation of the surfactant properties of ascorbyl palmitate sodium salt.
2002 Jul
[A case of renal pelvic tumor due to phenacetin abuse].
2002 May
Hydrogen bonding with adsorbent during storage governs drug dissolution from solid-dispersion granules.
2002 Nov
Interactions of human organic anion transporters and human organic cation transporters with nonsteroidal anti-inflammatory drugs.
2002 Nov
Phenotype of CYP2C19 and CYP3A4 by determination of omeprazole and its two main metabolites in plasma using liquid chromatography with liquid-liquid extraction.
2002 Nov 25
Hospitalized poisonings after renal transplantation in the United States.
2002 Nov 26
Mechanism-based inhibition of human liver microsomal cytochrome P450 1A2 by zileuton, a 5-lipoxygenase inhibitor.
2003 Nov
Assessment of tableting properties using infinitesimal quantities of powdered medicine.
2003 Sep 16
Phenacetin and cocaine in a body packer.
2004 Apr 20
Atomoxetine hydrochloride: clinical drug-drug interaction prediction and outcome.
2004 Feb
Six novel nonsynonymous CYP1A2 gene polymorphisms: catalytic activities of the naturally occurring variant enzymes.
2004 Jan
Antipyretic therapy.
2004 Jan 1
Validated assays for human cytochrome P450 activities.
2004 Jun
Evaluation of the Xpa-deficient transgenic mouse model for short-term carcinogenicity testing: 9-month studies with haloperidol, reserpine, phenacetin, and D-mannitol.
2004 Mar-Apr
[Prevention of bladder cancer].
2004 May
Patents

Sample Use Guides

In Vivo Use Guide
Analgesic mixtures containing phenacetin were previously marketed as tablets or capsules containing between 150 and 300 mg phenacetin. Common combinations were: 150 mg phenacetin, 230 mg aspirin, and 15 or 30 mg caffeine; or 150 mg phenacetin, 230 mg aspirin, 30 mg caffeine, and 8, 15, 30, or 60 mg codeine phosphate. Phenacetin alone was also available in 250 and 300 mg doses as tablets, and up to 500 mg doses as powder. The usual dose was 300 mg 4–6 times per day, and the daily dose was not to exceed 2 g
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:43:31 UTC 2019
Edited
by admin
on Tue Oct 22 00:43:31 UTC 2019
Record UNII
ER0CTH01H9
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHENACETIN
HSDB   INCI   INN   JAN   MART.   MI   VANDF   WHO-DD  
INN   INCI  
Official Name English
PHENACETIN [VANDF]
Common Name English
4-ETHOXY-1-ACETYLAMINOBENZENE
Systematic Name English
FENIDINA
Common Name English
NSC-7651
Code English
PHENACETIN [MART.]
Common Name English
ACETAMIDE, N-(4-ETHOXYPHENOL)-
Common Name English
PHENACETIN [JAN]
Common Name English
ACETPHENETIDIN
Common Name English
KALMIN
Common Name English
PHENACETIN [INCI]
Common Name English
PHENACETIN MELTING POINT STANDARD
USP-RS  
Common Name English
PHENACETIN [MI]
Common Name English
PHENACETINUM
HPUS  
Common Name English
PHENACETINUM [HPUS]
Common Name English
PHENACETIN [IARC]
Common Name English
PHENAZETIN
Common Name English
PHENACETIN [INN]
Common Name English
P-ACETOPHENETIDIDE
Common Name English
PHENACETIN MELTING POINT STANDARD [USP-RS]
Common Name English
PHENACETIN [HSDB]
Common Name English
ACETOPHENETIDIN
Common Name English
PHENACETIN [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC N02BE53
Created by admin on Tue Oct 22 00:43:31 UTC 2019 , Edited by admin on Tue Oct 22 00:43:31 UTC 2019
WHO-VATC QN02BE53
Created by admin on Tue Oct 22 00:43:31 UTC 2019 , Edited by admin on Tue Oct 22 00:43:31 UTC 2019
WHO-ATC N02BE03
Created by admin on Tue Oct 22 00:43:31 UTC 2019 , Edited by admin on Tue Oct 22 00:43:31 UTC 2019
WHO-VATC QN02BE73
Created by admin on Tue Oct 22 00:43:31 UTC 2019 , Edited by admin on Tue Oct 22 00:43:31 UTC 2019
IARC Phenacetin
WHO-ATC N02BE73
Created by admin on Tue Oct 22 00:43:31 UTC 2019 , Edited by admin on Tue Oct 22 00:43:31 UTC 2019
NCI_THESAURUS C45176
Created by admin on Tue Oct 22 00:43:31 UTC 2019 , Edited by admin on Tue Oct 22 00:43:31 UTC 2019
WHO-VATC QN02BE03
Created by admin on Tue Oct 22 00:43:31 UTC 2019 , Edited by admin on Tue Oct 22 00:43:31 UTC 2019
Code System Code Type Description
EVMPD
SUB09745MIG
Created by admin on Tue Oct 22 00:43:31 UTC 2019 , Edited by admin on Tue Oct 22 00:43:31 UTC 2019
PRIMARY
IUPHAR
7402
Created by admin on Tue Oct 22 00:43:31 UTC 2019 , Edited by admin on Tue Oct 22 00:43:31 UTC 2019
PRIMARY
CAS
62-44-2
Created by admin on Tue Oct 22 00:43:31 UTC 2019 , Edited by admin on Tue Oct 22 00:43:31 UTC 2019
PRIMARY
INN
412
Created by admin on Tue Oct 22 00:43:31 UTC 2019 , Edited by admin on Tue Oct 22 00:43:31 UTC 2019
PRIMARY
NCI_THESAURUS
C44432
Created by admin on Tue Oct 22 00:43:31 UTC 2019 , Edited by admin on Tue Oct 22 00:43:31 UTC 2019
PRIMARY
WIKIPEDIA
PHENACETIN
Created by admin on Tue Oct 22 00:43:31 UTC 2019 , Edited by admin on Tue Oct 22 00:43:31 UTC 2019
PRIMARY
HSDB
62-44-2
Created by admin on Tue Oct 22 00:43:31 UTC 2019 , Edited by admin on Tue Oct 22 00:43:31 UTC 2019
PRIMARY
RXCUI
8113
Created by admin on Tue Oct 22 00:43:31 UTC 2019 , Edited by admin on Tue Oct 22 00:43:31 UTC 2019
PRIMARY RxNorm
ChEMBL
CHEMBL16073
Created by admin on Tue Oct 22 00:43:31 UTC 2019 , Edited by admin on Tue Oct 22 00:43:31 UTC 2019
PRIMARY
MESH
D010615
Created by admin on Tue Oct 22 00:43:31 UTC 2019 , Edited by admin on Tue Oct 22 00:43:31 UTC 2019
PRIMARY
EPA CompTox
62-44-2
Created by admin on Tue Oct 22 00:43:31 UTC 2019 , Edited by admin on Tue Oct 22 00:43:31 UTC 2019
PRIMARY
MERCK INDEX
M8589
Created by admin on Tue Oct 22 00:43:31 UTC 2019 , Edited by admin on Tue Oct 22 00:43:31 UTC 2019
PRIMARY Merck Index
ECHA (EC/EINECS)
200-533-0
Created by admin on Tue Oct 22 00:43:31 UTC 2019 , Edited by admin on Tue Oct 22 00:43:31 UTC 2019
PRIMARY
PUBCHEM
4754
Created by admin on Tue Oct 22 00:43:31 UTC 2019 , Edited by admin on Tue Oct 22 00:43:31 UTC 2019
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
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METABOLITE ACTIVE -> PARENT
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METABOLITE TO PARENT DRUG RATIO
PLASMA; URINE
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ACTIVE MOIETY